


A Kiss Goodbye

by LaserMumu



Category: Supernatural
Genre: Demon Dean Winchester, Demon Sex, Evil Dean Winchester, Hurt Crowley (Supernatural), Hurt Jack, Hurt Sam Winchester, M/M, Mark of Cain (Supernatural), Nonconsensual Underage Sex, Nudes, Sad Crowley (Supernatural), Scared Jack Kline, Smut, Suicidal Dean Winchester, Underage Rape/Non-con, Underage Sex
Language: English
Status: Completed
Published: 2020-05-07
Updated: 2020-05-11
Packaged: 2021-03-03 01:14:34
Rating: Explicit
Warnings: Rape/Non-Con, Underage
Chapters: 3
Words: 2,862
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24056548
Author URL: https://archiveofourown.org/users/LaserMumu/pseuds/LaserMumu
Summary: ⚠️EXPLICIT⚠️ Dean is still not over Crowley's death and what he did to him. During one of Dean's messy nights, Jack just happens to have a nightmare when Sam's recovering from a bad hunt.
Relationships: Castiel/Sam Winchester, Crowley (Supernatural)/Dean Winchester, Jack Kline/Dean Winchester, Jack Kline/Sam Winchester
Comments: 2
Kudos: 32





	1. Thoughts

**Author's Note:**

  * For [LaserV](https://archiveofourown.org/users/LaserV/gifts).



> There is a copy of this (my) story on Wattpad. If you want to, you can paste this link into a search engine.
> 
> Wattpad Copy: https://www.wattpad.com/myworks/224120124-a-kiss-goodbye

Dean stared at a selfie of him and Crowley, who was now deceased. Dean’s mouth was dry, and his eyes were bloodshot and puffy. Sure, Crowley was smiling in the photo, but his eyes were dead and he was broken. Dean thought about how he made that man cry, beg, and bleed. He bruised him and licked the blood of Crowley’s arms when he found Crowley cutting himself in the bathroom of their then shared motel room. He was a demon back then, though. Dean told himself that it was the Mark of Cain that led Dean to do this, it wasn’t him, but it was. Dean sobbed when he thought of all the times he had raped Crowley even when Crowley’s asshole began to bleed. He gave it to Crowley dry, and his cocked hardened at Crowley’s cries. Sometimes Crowley had just let Dean have his way with him and took the pain, not saying or doing anything against it. Dean thought of the times he made Crowley get on his hands and knees, butt naked, and whipped his bare bottom with a belt. Dean sobbed into his pillow, letting out a wail. Dean knew what Crowley was experiencing. He knew he was living all those moments again in the empty. Dean knew that Crowley was internally screaming. 

Sam was worried about Dean. He heard Dean cry at night. He heard him take his nightly journey to the bathroom. Sa, assumed it was to pee until he walked by to go to the kitchen for water. He had heard a blade being placed in the sink counter. While Dean thought of the horrible things he had done with Crowley, the physical and emotional pain he had inflicted to make Crowley suicidal, he stroked himself. The thought of Crowley on his knees, a bloody and bruised mess, sobbing, begging, Dean to stop before Dean shoved his cock into his mouth was so fucking sexy to Dean. Dean, butt naked,laid on his messy bed, the blanket and sheet beneath him. Dean felt his eyes burn as he jerked himself off harder and thought of the words he had called Crowley before, during, and after sex.

“Slut.”

“Whore.”

“Faggot.”

He had told Crowley that he deserved this, that he was being punished for his cruel deeds. Dean knew Crowley wanted to die, and he knew that he was adding fuel to the fire, but back then, he didn’t give a fuck. When Crowley had come out to Dean, Dean just rolled his eyes and said “whatever”. After the mark of Cain, Crowley had come to Dean for metal help, as he didn’t want to talk to anyone else. Dean had just smacked him and told him off, saying that he “only wanted attention,” and to “get the fuck out of his face.” Crowley had only nodded before hurrying off. He never spoke about it to anyone after that. Dean,new he was a monster. He had picked out every one of Crowley’s flaws. He squeezed Crowley’s stomach, making fun of his weight. He knew that overeating was a coping mechanism for Crowley. When Crowley told Dean that he had been born a girl, Dean said nothing. He started calling Crowley “tranny”. 

Dean had started hallucinating. He saw Crowley on his knees, all torn up, sobbing, begging Dean to stop. Dean heard whispers. A British accent, Crowley’s voice, saying “Bye boys” at random times of the day. Crowley was in his dreams. Well, they were more like nightmares. Dean started not sleeping. The only times he’d come out of his room were to get more food, go to the bathroom, or help on a hunt. He didn’t even perform well on the hunts. Dean felt his cock grow rock hard when he thought of one of his favorite moments in a motel room with Crowley. 

—————————————————————————————————————————————————————————

Crowley clenched his teeth as he heard Dean call him names. He was not a slut. He was not a whore. He heard Dean call him homophobic and transphobic slurs maybe fifteen times a day, the rest of the day were other words. Crowley boiled with rage. He looked Dean right in the eye and began cussing him out in French, English, and Latin. He was screaming until he smacked Dean right across the face. This angered Dean. He stripped Crowley of all clothes and pinned him against the wall, his bare ass facing Dean. Dean slid open a drawer and took out a belt. He positioned himself in the right stance, and brought the belt to Crowley’s cheeks until they were bright red. Dean grabbed Crowley’s face and brought a fist the the side of his skull, right by the eye. A few moments later, and Crowley was a bruised, bloody, sobbing, broken mush in Dean hands. Dean dropped Crowley to the floor. Crowley was lying on the tough wooden floor. Dean dropped down and positioned his groin in front of Crowley’s mouth. Dean stuffed his hard erection in Crowley’s mouth. He heard a gag from the smaller man who soon began to wheeze. Dean pulled Crowley’s right arm to his asshole when he felt that Crowley could move his arms. Dean took Crowley’s hand and shoved his fingers into his asshole. Dean moaned as he felt himself dump a load down Crowley’s throat. He pulled out. Crowley turned his head and all the cum came spilling out. Crowley vomited an icky pale cream colour onto the floor. Dean smacked Crowley across the face. He gathered the still numbers mush of Crowley and molded him onto his hands and knees. Crowley’s head faced the vomit and Dean!s cum. Dean separated Crowley’s bleeding, puffy, swollen lips and pulled his tongue out. Dean pushed Crowley’s head down towards the mess and collapsed next to Crowley, stroking himself as he watched Crowley lick up the mess. The tase was foul, causing Crowley to swallow another batch of vomit. 

——————————————————————————————————————————————————————————

Dean jerked himself off, tears still swimming down his cheeks. He the heard the door creak open.


	2. All Mine

**Summary for the Chapter:**

> Jack has a nightmare, but Sam and Cas... aren’t available. So he goes to Dean’s room. Oh, how he wishes he hadn’t.

**Notes for the Chapter:**

> To see this story on Wattpad, there is a link on the first chapter. You can copy and paste it into a search engine if you want to. Also, I am not sitting on Dean, k really love him, but this idea was too much for me not to write so... :) here it is.

Jack woke up panting. He was seating and shaking, the horrifying images of monsters in his head. Jack looked around the room. He was in bed, there were no monsters. Jack cautiously got up from the messy bed and walked towards the door. Jack crept down the hallway. He was right outside of Sam’s room when he remembered that Sam had been seriously injured on a hunt with something Cas could not magically heal, and it was too dangerous for Jack to use his magic on Sam. Jack heard Cas from the room.

“It’s okay, sweetheart. I know everything hurts, but it will all be better soon.” Cas’ words were comforting. Then Jack heard Sam. He heard Sam moan Cas’ name. Jack’s eye flowed yellow as his sight flew behind the door. Sam’s pants were on the floor, and his boxers were pulled to his knees. His dick was lathered in lube and a fully clothed Cas was caressing Sam’s pee hole. Sam whined, wanting more. Cas just hushed him and grabbed a hanker chief from his trench coat’s inside pocket. He wiped the lube from Sam’s hard shaft. Cas slipped Sam’s penis into his mouth. Sam moaned as Cas tongued his pee hole. The bottle of lube was next to Cas, and it had no lid. Cas brought his left arm over Sam’s chest and dipped two finger s into the bottle of lube. Cas slipped half of Sam’s length down his throat as he stuck his two fingers into Sammy’s hole Sam moaned. His body hurt, but his groin was filled with immense pleasure. Cas gagged as he took a little more of Sam’s cock. Sam grabbed Cas’ head and pushed it down, causing Cas to choke and gag. The sounds only made Sam harder. Jack’s eyes went back to normal. He almost threw up. He did not want to see his dad and secret lover doing those things. Jack turned in his heel and was going back to his room when he saw the monsters again. It must’ve been his mind but he was still scared straight out of his mind. Jack crept down the hallway and to Dean’s room. It was not very likely that Dean would let Jack sleep with him, but it was worth a shot. Jack creaked the door open. Jack’s eyes widened and his eyebrow raised. Dean was butt naked on his bed, sobbing, and... jerking off? Dean’s phone showed a picture of him and an older, shorter man. 

“Dean?” Jack’s voice cracked. Dean turned to face Jack.

“Hey, Jackie.” Dean croaked. 

“What’s wrong?” Jack asked,taking a step into the room.

“I-I was just thinking about an old friend.” Dean replied.

“And jerking off to their picture?” Jack could only assume that the man in the picture was the friend they were talking about.

“Yes... we had... benefits.” Dean explained. 

“Oh.” Jack whispered. “May I come in?” Dean nodded. Jack came in and sat on the bed.

“What was his name?” Jack asked. 

“Crowley. He was Rowena’s kid.” Dean answered.

“What happened to him?” Jack asked.

“He- he sacrificed himself...” Dean stuttered.

“Oh... I’m sorry for bringing it up, Dean. I didn’t know-“ Jack was cut off when Dean planted a kiss on his lips. Jack’s mouth dropped slightly. Dean was over thirty-five, and Jack was only a few months old. 

“It’s okay.” Dean spoke. “He wanted to die...”

“He wanted to die? Why?” Jack asked. 

“I did... terrible things to him. He was broken before we met, but I had completely shattered him.” Dean explained, hi voice trailing off.

“I hope you don’t mind... but can I know what you did to him?” Jack asked, already prepared for Dean to slap him. Dean didn’t, you wouldn’t hit someone you want something from. 

“How about I show you?” An evil grin grew on Dean’s face. Jack raised a brow, but nodded.

“Okay...” Jack said slowly. Dean picked up his phone. He entered a photo album which Jack couldn’t see the title of. The almighty was full of naked pictures of this man. Some he looked dead inside, some he was crying. He was bleeding and bruised in these photos. He was tied up and looked so scared. Jack began to stutter. Tears began to from in his eyes.

“D-Dean... why would you do that...?” Jack stuttered. Dean completely ignored the question.

“I did other things.” Dean whispered, his hand resting on Jack’s clothed groin. 

“What did you do, Dean?” Jack peeped. He kind of didn’t want to know, but he also wanted to. 

“I fucked him, Jack. I raped the shit out of him, and I would do it again. He was so small, short... He couldn’t fight back.” Jack saw Dean’s dick tense up as he spoke. His hand trailed upwards to Jack’s stomach. “I beat him, Jack. I made him lick up his own puke. I practically owned him, Jackie.” 

Dean propped himself up on his elbow. He towered over Jack, who was shaking beneath the older man. 

“I made him cut himself in front of me, Jack, and I would lick up the blood, oh, you don’t know how much I miss him.” Dean growled. He slid his thumb under the top of Jack’s leggings. 

“You remind me so much of Adam.” Dean told Jack.

“Who’s Adam?” Jack asked, his voice shaky.

“He’s my little half-brother. He was such a slut for me, craving my love so much, he’d spread his legs wide for me. He was so flexible, Jackie. Then I left him to rot in Hell.” Dean’s voice was grim. Jack’s breathing grew heavy. He needed to get out of there. He felt something clasp around his wrist. A cuff that could only be removed from the rust by the person who put it there, and blocked anything from using it’s magic. 

“You’re all mine tonight, Jackie.” Dean whispered into Jack’s ear, sending chills down Jack’s spine.


	3. “This”

**Summary for the Chapter:**

> Jack’s words caused Dean’s eyes to widen
> 
> “I want this.”

**Notes for the Chapter:**

> This is the final chapter as of now, and most likely forever. There is link you can copy and paste into a search engine on the first chapter if you want to check out the Wattpad copy. There is smut on this, so if you don’t feel comfortable, don’t read it.

Dean caressed Jack’s groin.

“Dean, please-“ Jack tried to say, but he was cut off by Dean’s lips. Jack pushed Dean away.

“I don’t want this!” Jack tried to get up, but Dean grabbed his hair. Dean pulled Jack down on the bed, causing a yelp to come from, the younger, smaller boy.

“You’re more of a fighter than I anticipated, Jackie, but you’re going to obey my commands. Now stay still.” Dean smiled.

“No!” Jack exclaimed, pushing Dean away again. Dean gripped Jack’s shirt collar and pulled him close.

“It wasn’t a request, Jack. It’s a command.” He growled. Jack’s breathing grew heavier. “Now show me your body.” Dean reached under his bed and took out a belt. This time, Jack obeyed. He peeled off his shirt. Dean stared at Jack’s nipples, licking his lips. Jack whimpered as he saw the bulge in Dean’s jeans grow. Jack slipped off his leggings, revealing his satin, orange-red, panties. Jack peeled his socks off with his feet. Dean rested his hand on Jack’s clothed crotch. His erection hardened as he felt Jack’s penis through the thin, soft fabric. Dean pulled out his phone. He pulled the blanket off of Jack and started snapping photos of the half-naked child before him. Dean placed his phone of the nightstand. Dean stripped himself of all clothing. He got onto the bed. Dean crawled towards Jack. Dean placed his lips around Jack’s right nipple and slowly began to suck on it like a pacifier. 

“Dean...stop. I don’t want to do this.” Jack spoke. In response, Dean bit down on the sensitive nub on Jack’s nipple. Jack yet out a cry of pain, understanding that Dean was telling him that he didn’t have choice.

“Yes, Dean.” Jack mumbled in response to the bite. Dean bit down again, causing tears to swell in Jack’s eyes. Dean lifted his head up.

“Listen here, slut. In the bedroom, you will not address me by name. Let’s try again.” 

“Yes...” Jack sighed. “Master.”

“Better.” Dean smiled as he went back to work. Dean, not breaking contact with Jack’s nipple, pulled the smaller boy on top of him. Dean pressed his hard, naked shaft against Jack’s clothed cock. Dean moved to Jack’s left nipple and began to work on it. Dean stopped.

“Take em’ off, slut.” Dean commanded. Jack hesitated. “Take. them. off.” Dean repeated, angrily. Jack whimpered, sliding the pair of panties down his legs and off his body. “Listen here, whore. This is completely consensual, okay? You belong to me.” Dean told Jack. Jack nodded, though it wasn’t consensual. Jack didn’t want this. 

“Touch my dick, slut. I know you want it.” Dean commanded. Jack obeyed and began stroking Dean’s hard cock. 

“Tell me you like it.” Dean demanded.

“I-I like it.” Jack obeyed. Dean locked eyes with the child on top of him.

“Tell me you love it.” He whispered.

“I love it.” Jack forced himself to speak.

“Where do you want it?” Dean asked.

“Inside me!” Jack whined. Dean teased Jack’s entrance. Something inside Jack changed. He looked Dean straight in the eyes and changed his mind.

“I want this.”

This surprised Dean, but he was happy that Jack did. Dean sat up, Jack on his lap. 

“Lube?” Jack’s eyebrow raised. Dean shook his head.

“Dry.”

Jack lifted his ass and propped Dean’s dick up. Dean looked up at Jack.

“Fuck yourself on my cock. Tell me how it feels.” 

Jack sat down on Dean’s dick. Jack shot up a little in pain, but Dean pressed him down. Jack began to bounce up and down, searching for his own prostate.

“How does it feel?” Dean asked. Jack went faster.

“It hurts. Your so...” Jack cut himself with a moan. “Big, Master.” Jack then moaned. Dean grabbed Jack’s cock and began running his thumb up and down Jack’s pee hole. Jack moaned. Dean pushed Jack down on the bed. The pillows were now behind them. Dean thrusted into Jack’s asshole, the sound of their skin slapping together only got Jack harder. Dean smacked Jack across the face, causing Jack’s penis to become fully erect. Jack grabbed the back of Dean’s shoulders and pulled him down. Jack began to suck on Dean’s right nipple, his right hand playing with the other Dean moaned. Jack stopped sucking and instead began playing with it using his left hand. Dean propped himself on his hiss left arm and began jerking Jack off. Jack felt his dick begin to twitch. Dean and Jack looked into each other’s eye’s helplessly as Dean felt his hand sodden. 

Jack and Dean fell back onto the bed, their heads molding the pillows to hold them. Dean’s wet hand stuck on Jack’s lips. Jack separated his lips to let Dean’s pointer finger in. Dean let out a quiet moan. Jack welcomed Dean’s middle finger, fulfilling Dean’s kink. Soon, all of Jack’s semen was licked up and Dean’s sheets were wet. Dean moved closer to Jack and planted a kiss on Jack’s lips. Jack smiled when Dean pulled back and lifted his head to return the favor. Jack poofed his clothes on. Jack planted another little kiss on Dean’s lips and whispered.

“Goodbye.”


End file.
